On one morning of 1965, an explosion went off in University Circle. The source of the explosion were two dynamite sticks placed in the kitchen vent of the Jazz Temple. Winston, 23 years old at the time, would wake to find his thriving jazz business had been forced to close seemingly overnight. This wouldn’t be the last time that Winston’s properties would be destroyed, but these acts would not mark the end of Winston’s entrepreneurial spirit in the Cleveland area. In fact, it was just the beginning.

Winston arrived in Cleveland in 1958 by the way of Detroit, Michigan. Already a trained manager and entrepreneur, he set his sights on creating his own thriving businesses. Winston was a talker and made friends as soon as he arrived in Cleveland, even becoming close with Carl Stokes prior to his mayorship. The people who knew him described him as charismatic, confident, black business man.

When Winston arrived in the Cleveland area, he found that the East Side was struggling economically, especially the predominantly-black community of Glenville. He set up shop in the area and opened three businesses in the span of five years: The Jazz Temple, a jazz coffeehouse; Winston’s Place, a fine-dining establishment; and Scrumpy-Dump, a local cinema.

It was around this time that Winston’s name began to appear in local publications such as the Call and Post and the Plain Dealer. The Plain Dealer presented him as “Cleveland’s Porno King” due to the nature of films played in his cinema, but getting big-name films were hard at the time for a smaller cinema, especially for black owners.

“It wouldn’t have been necessary for us to deal with so-called pornography if blacks had been able to have real relationships with banks and lending institutions,” wrote Elmer Turner, vice president of the University Circle Property Development, in a Cleveland Press article entitled “Brave New World of Winston Willis.”

Once Winston had access to more wealth, the films offered at the cinema changed. It hosted screenings of blaxploitation films that were popular in the early 1970s that brought in large crowds. Winston’s sister Aundra remembers managing the concession stand the opening day of Super Fly.

“I went to work early when I came down and turned down on Euclid Avenue,” she said. “There was a line waiting outside of the theatre and around the block. I wanted to turn around and go home.”

Winston was inside of the building sending out workers to buy more popcorn and hot dogs for the hungry, waiting crowd. However, none of this would have happened if it weren’t for a few lucky nights amid some chaotic times in Cleveland.

In the late evening of July 27, 1968, the city of Cleveland was held together by martial law after the Glenville shootout. Close by, Winston emerged from a three-night gambling session in the back room of his late-night restaurant Hot Potato with $500,000 in cash in two trash bags. He had won the money against six other gentleman, including a notable pimp named Git. In the end, Winston’s luck ran so hot that his fellow gamblers called him the “negro with the magic hands.”

As Winston earned his winnings, his neighborhood swarmed with national guard and cops. Aundra describes that night as one of fear from the shootings, the joy of a new baby, and how small knocks on her front door woke her from her sleep. Winston had driven home and then to Aundra’s in a white jaguar convertible, where he brought money for her to deposit in different banks around the city. Aundra agreed.

Winston used his winnings to buy properties between 105th and 107th streets and Euclid Avenue. At first, he faced issues with the Cleveland Trust Company, which he believed wouldn’t sell him property due to his race. After some finagling, including setting up an adult bookstore in an abandoned building, Winston acquired most of the properties. It was at this point when Winston began to expand and build his “Miracle on 105th” and the “inner-city Disneyland.”

The string of properties included more than 23 businesses, including an arcade, bookstores, and other various shops. Winston’s properties also housed The University Circle Property Development, an organization created to continue entrepreneurial ventures in the community through a black-led organization. Winston told reporters Emmanuel Hughley, Jr. and Dick McLaughlin of the Cleveland Press that his businesses made him the city’s biggest employer of black people in Cleveland.

“I grew up in that area; it was a hustling type community,” says Johnnie Johnson, an East Cleveland native. “It was the black people’s downtown. Instead of us going downtown, we went to 105th. Everything you wanted was on 105th.”

Winston told the Cleveland Press that he just humanized the space and made it something people wanted. With the steady progress and reinvestment from both black and white Clevelanders, the UCPD and Winston’s opportunity corridor should have been admired and upheld by the city. However, buying up the property made Winston a target.

There were numerous fire inspections of his properties. Winston faced threats to both his life and businesses, and police were routinely in his locations. Winston could have kept his head down or left the business while he was ahead. Instead, he started to speak openly about what he felt were attacks on him just for his race by placing hand-drawn billboards on the side of his building.

These billboards called out the city and even specific people. Winston got a local street artist named Mike Kirpatrick, a man who Winston had allowed to do portraits in his nightclubs and had seen around the neighborhood. The images ranged from Winston facing off prosecutors to blocks of texts calling for out racism in the city.

“[Winston] would tell me what he wanted and I would draw it,” Mike said. “One he had…I think his name was Corrigan. He wanted black people hanging Corrigan.”

Indeed, Mike drew former Prosecutor Attorney John T. Corrigan being hanged by black people with the devil laughing at his back. However, Mike also made sure to mention that it was Winston’s interpretation and that he just drew it. Corrigan had been trying to bring an organized crime charge against Winston. The charges were eventually dismissed, but that didn’t stop the heated tension noted in newspapers during the time.

Winston’s empire all came crashing down due to a single check. In 1983, Winston was sentenced to a year in prison for a check worth a little more than $400. The check had been made to a lumber company, but it had bounced. Aundra alleges that Winston himself had never even signed it. Instead, she claims Winston’s Chief Financial Officer Elsayed Aly Ayoub had signed the check instead.

Despite this, Case Western Reserve University Law Professor Spencer Neth was able to prove that Winston shouldn’t have been convicted because the check was initially approved by the bank and should have cleared according to banking laws at the time. While imprisoned, many of his properties were seized and torn down to make room for Cleveland Clinic to expand. According to his sister, the buildings were torn down swiftly with no news coverage and Cleveland Police surrounding the area.

Winston filed a lawsuit against the city, Cleveland Clinic, University Circle, and numerous other entities in 1977, but it went nowhere. His final billboard set the tone for the future of University Circle.

“Farewell Friend & Neighbor. After 10 years serving this community soon we must close our businesses to make way for …. U.C.I – Cleveland Clinic – State of Ohio …. To Build a New Hospital for Whites”

“I did see when the area changed,” Johnson said. “He was forced out by the Cleveland Clinic. The Cleveland Clinic started buying up everything there, which they are still doing today.”

Winston didn’t leave Cleveland after his thriving businesses were torn down. Though he’s stepped out of the city’s spotlight, Winston didn’t back down. He took his fight against wrongful property seizures and foreclosures to the court system. After his appeals to the City of Cleveland’s court, Winston and Aundra petitioned the Supreme Court to review his case. It was denied in 2007.

If you take a walk down Euclid Avenue today, you won’t see a single marker of Winston’s businesses. No billboards, no scrumpy-dump cinemas with lines wrapped around the corners waiting for the next blaxploitation film to open. The street is no longer a bustling black entertainment hub. All the remains are blocks full of medical buildings and the fading memories of the Miracle on 105th.